How can I simulate cloth between one static object and one moving object?
You can do it this way:

Create your sail and a create a bone that you call Bone1:



Give your sail a vertex group that will be the cloth pin (call this group Pin), it must be all around the border:



Give your sail a vertex group for the bone control (call this group Bone1) that must have a decreasing influence:



Give your sail a Cloth physic simulation. In the Cloth panel &gt; Shape, choose the group you've created as Pin Group, enable Self Collisions. Select the vail, shift select the bone, switch it to Pose mode, and press CtrlP &gt; Set Parent To &gt; Armature Deform so that the bone will control the vertex group that has its name. Create the rest of the object, give it Collision physic if it is supposed to interact with the vail: